Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:28:15 UTC |
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Update Date | 2014-12-24 20:25:54 UTC |
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Accession Number | T3D2969 |
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Identification |
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Common Name | Rifampin |
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Class | Small Molecule |
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Description | A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160) |
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Compound Type | - Amide
- Amine
- Antibiotic
- Antibiotic, Antitubercular
- Antitubercular Agent
- Antituberculosis Agent
- Drug
- Enzyme Inhibitor
- Ester
- Ether
- Hydrazine
- Leprostatic Agent
- Metabolite
- Nucleic Acid Synthesis Inhibitor
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 3-(((4-Methyl-1-piperazinyl)imino)methyl)rifamycin sv | RFP | Rifadin | Rifadine | Rifaldin | Rifampicin | Rifampicina | Rifampicinum | Rifoldin | Rimactan | Rimactane | Rofact | Tubocin |
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Chemical Formula | C43H58N4O12 |
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Average Molecular Mass | 822.940 g/mol |
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Monoisotopic Mass | 822.405 g/mol |
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CAS Registry Number | 13292-46-1 |
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IUPAC Name | (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,21Z)-2,15,17,23,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{[(4-methylpiperazin-1-yl)imino]methyl}-6-oxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-13-yl acetate |
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Traditional Name | (7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,21Z)-2,15,17,23,27,29-hexahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{[(4-methylpiperazin-1-yl)imino]methyl}-6-oxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,23,25(29),26-nonaen-13-yl acetate |
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SMILES | [H]C(=NN1CCN(C)CC1)C1=C(O)C2=C3C(O)=C(C)C4=C2C(=O)[C@](C)(O4)O\C([H])=C([H])/[C@]([H])(OC)[C@@]([H])(C)[C@@]([H])(OC(C)=O)[C@]([H])(C)[C@]([H])(O)[C@]([H])(C)[C@@]([H])(O)[C@@]([H])(C)C([H])=C([H])\C([H])=C(C)/C(O)=NC1=C3O |
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InChI Identifier | InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14-,22-13-,44-20-/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1 |
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InChI Key | InChIKey=JQXXHWHPUNPDRT-XHVADFQNSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Naphthofurans |
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Sub Class | Not Available |
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Direct Parent | Naphthofurans |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 183°C | Boiling Point | Not Available | Solubility | 1400 mg/L (at 25°C) | LogP | 2.7 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-19 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-19 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-19 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-19 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-10-19 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | 2021-10-19 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-08fr-0500000980-bcda18a9b24d3d79bd0f | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06re-2000002920-94cf3ba1024f60e0d138 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fu-9100004200-9e06a013254c65e92b1b | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-3000001890-0f3bb09775c02b839efd | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fr-6400004940-8b7df11383262cc72600 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a7l-9000006400-07b6061e661dceef4411 | 2017-09-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05fs-0000000980-cb73939dde5e32bb8f04 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-08mj-0000000920-d46bb707a0a349fd5104 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0aor-9000001720-cfb21aab6c00cbf1ceba | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-1000001970-fb31d2ee3ab42795a510 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9000000000-c78a5fe9b5c2c64d82b7 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0aba-6100009620-791625018751337a6228 | 2021-10-11 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral. Well absorbed from gastrointestinal tract. |
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Mechanism of Toxicity | Rifampin acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death. |
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Metabolism | Primarily hepatic, rapidly deacetylated.
Route of Elimination: Less than 30% of the dose is excreted in the urine as rifampin or metabolites.
Half Life: 3.35 (+/- 0.66) hours |
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Toxicity Values | LD50: 1570 mg/kg (Rat) (1) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | 3, not classifiable as to its carcinogenicity to humans. (5) |
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Uses/Sources | For the treatment of Tuberculosis and Tuberculosis-related mycobacterial infections. |
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Minimum Risk Level | Not Available |
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Health Effects | Antibiotic resistance |
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Symptoms | Chronic exposure may cause nausea and vomiting and unconsciousness |
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Treatment | Intensive support measures should be instituted and individual symptoms treated as they arise. Since nausea and vomiting are likely to be present, gastric lavage is probably preferable to induction of emesis. Following evacuation of the gastric contents, the instillation of activated charcoal slurry into the stomach may help absorb any remaining drug from the gastrointestinal tract. Antiemetic medication may be required to control severe nausea and vomiting. Active diuresis (with measured intake and output) will help promote excretion of the drug. Hemodialysis may be of value in some patients. (4) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01045 |
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HMDB ID | HMDB15179 |
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PubChem Compound ID | 5381226 |
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ChEMBL ID | CHEMBL374478 |
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ChemSpider ID | 10468813 |
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KEGG ID | C06688 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 28077 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Rifampin |
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PDB ID | RFP |
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ACToR ID | Not Available |
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Wikipedia Link | Rifampin |
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References |
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Synthesis Reference | Klaus Jurgen, Joachim Seydel, “Combination preparations containing rifampicin and thioacetazon.” U.S. Patent US5104875, issued August, 1973. |
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MSDS | Link |
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General References | - Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
- Baysarowich J, Koteva K, Hughes DW, Ejim L, Griffiths E, Zhang K, Junop M, Wright GD: Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr. Proc Natl Acad Sci U S A. 2008 Mar 25;105(12):4886-91. doi: 10.1073/pnas.0711939105. Epub 2008 Mar 18. [18349144 ]
- Drugs.com [Link]
- RxList: The Internet Drug Index (2009). [Link]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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Gene Regulation |
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Up-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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Down-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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